CA2184433A1 - Retinoid Formulations in Porous Microspheres for Reduced Irritation and Enhanced Stability - Google Patents
Retinoid Formulations in Porous Microspheres for Reduced Irritation and Enhanced StabilityInfo
- Publication number
- CA2184433A1 CA2184433A1 CA2184433A CA2184433A CA2184433A1 CA 2184433 A1 CA2184433 A1 CA 2184433A1 CA 2184433 A CA2184433 A CA 2184433A CA 2184433 A CA2184433 A CA 2184433A CA 2184433 A1 CA2184433 A1 CA 2184433A1
- Authority
- CA
- Canada
- Prior art keywords
- porous microspheres
- enhanced stability
- reduced irritation
- retinoid formulations
- retinoid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/07—Retinol compounds, e.g. vitamin A
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/0279—Porous; Hollow
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
Abstract
Retinoids for topical skin application are formulated as impregnants in porous microspheres. Thus formulated, the retinoids display a surprisingly high level of stability and low degree of skin irritation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/581,126 US5851538A (en) | 1995-12-29 | 1995-12-29 | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
US08/581,126 | 1995-12-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2184433A1 true CA2184433A1 (en) | 1997-06-30 |
CA2184433C CA2184433C (en) | 2000-01-18 |
Family
ID=24323987
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002184433A Expired - Lifetime CA2184433C (en) | 1995-12-29 | 1996-08-29 | Retinoid formulations in porous microspheres for reduced irritation and enhanced stability |
Country Status (11)
Country | Link |
---|---|
US (1) | US5851538A (en) |
EP (1) | EP0781551B1 (en) |
JP (1) | JP2960022B2 (en) |
KR (1) | KR100262117B1 (en) |
AT (1) | ATE209032T1 (en) |
AU (1) | AU697584B2 (en) |
CA (1) | CA2184433C (en) |
DE (1) | DE69617181T2 (en) |
DK (1) | DK0781551T3 (en) |
ES (1) | ES2168414T3 (en) |
PT (1) | PT781551E (en) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2774907B1 (en) * | 1998-02-19 | 2000-05-12 | Luc Dewandre | NEW TOPICAL FORMULATION BASED ON RETINALDEHYDE |
TWI234455B (en) * | 1998-04-02 | 2005-06-21 | Univ Michigan | Methods and compositions for reducing UV-induced inhibition of collagen synthesis in human skin |
US6683069B1 (en) | 1998-04-02 | 2004-01-27 | Regents Of The University Of Michigan | Methods and compositions for reducing UV-induced inhibition of collagen synthesis in human skin |
US5891470A (en) * | 1998-04-17 | 1999-04-06 | Advanced Polymer Systems, Inc. | Softgel formulation containing retinol |
US6228894B1 (en) * | 1998-04-17 | 2001-05-08 | Enhanced Derm Technologies, Inc. | Softgel-compatible composition containing retinol |
BR9803936A (en) | 1998-09-08 | 2000-04-04 | Cosmeticos Natural Ind Com | Process and composition to increase the action of vitamin A on an individual's cellular activity and use of vitamin C. |
US6194006B1 (en) * | 1998-12-30 | 2001-02-27 | Alkermes Controlled Therapeutics Inc. Ii | Preparation of microparticles having a selected release profile |
US7758888B2 (en) * | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
EP1335693A2 (en) | 2000-04-21 | 2003-08-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
EP1278504A2 (en) * | 2000-05-05 | 2003-01-29 | R.P. Scherer Technologies, Inc. | Oil-in-water emulsion formulation containing hydroquinone and retinol |
US6896890B2 (en) * | 2000-05-05 | 2005-05-24 | R.P. Scherer Technologies, Inc. | Oil-in-water emulsion formulation containing free and entrapped hydroquinone and retinol |
US6896905B2 (en) * | 2001-02-15 | 2005-05-24 | Rohm And Haas Company | Porous particles, their aqueous dispersions, and method of preparation |
US6590059B2 (en) | 2001-05-11 | 2003-07-08 | Ap Pharma, Inc. | Bioerodible polyorthoesters from dioxolane-based diketene acetals |
EP1304161B1 (en) * | 2001-10-19 | 2007-02-28 | Pacific Corporation | Thermotropic liquid crystal polymer microcapsules, a method for preparing the same, and cosmetic compositions containing the same |
US6524606B1 (en) | 2001-11-16 | 2003-02-25 | Ap Pharma, Inc. | Bioerodible polyorthoesters containing amine groups |
US20030232091A1 (en) * | 2002-06-17 | 2003-12-18 | Adi Shefer | Stabilized retinol for cosmetic dermatological, and pharmaceutical compositions, and use thereof |
EP1590009B1 (en) * | 2002-10-22 | 2012-06-06 | Allegiance Corporation | Coating composition for skin-contacting surface of elastomeric articles and articles containing the same |
CN100462070C (en) * | 2003-06-30 | 2009-02-18 | 于美丽 | Retinoic acid release control nanomicrosphere and its preparation method |
US20050002996A1 (en) * | 2003-07-02 | 2005-01-06 | Milan Sojka | Sustained release compositions and controlled delivery method |
AU2003292509B2 (en) * | 2003-12-15 | 2007-08-02 | Council Of Scientific And Industrial Research | Taste masked pharmaceutical compositions comprising bitter drug and pH sensitive polymer |
CA2549539C (en) | 2003-12-15 | 2013-02-12 | Council Of Scientific & Industrial Research | Taste masked pharmaceutical composition comprising ph sensitive polymer |
CN100548270C (en) * | 2004-12-10 | 2009-10-14 | 科学与工业研究委员会 | Improve Pharmaceutical composition of palatability of drugs and preparation method thereof |
JP2009221164A (en) | 2008-03-17 | 2009-10-01 | Nitto Denko Corp | Drug for treating pulmonary fibrosis |
US20120269886A1 (en) | 2004-12-22 | 2012-10-25 | Nitto Denko Corporation | Therapeutic agent for pulmonary fibrosis |
PL1842557T3 (en) | 2004-12-22 | 2014-04-30 | Nitto Denko Corp | Drug carrier and drug carrier kit for inhibiting fibrosis |
KR101158162B1 (en) * | 2005-08-02 | 2012-06-19 | 솔-겔 테크놀로지스 리미티드 | Metal oxide coating of water insoluble ingredients |
JP5342834B2 (en) * | 2008-09-05 | 2013-11-13 | 日東電工株式会社 | Treatment agent for myelofibrosis |
US9572886B2 (en) | 2005-12-22 | 2017-02-21 | Nitto Denko Corporation | Agent for treating myelofibrosis |
US20080020023A1 (en) | 2006-07-20 | 2008-01-24 | Shiping Wang | Nonaqueous coating composition for elastomeric articles and articles containing the same |
MXPA06008988A (en) * | 2006-08-08 | 2008-02-07 | Fernando Ahumada Ayala | Topical antiacne preparations containing retinoid (tazarotene or adapalene), antibiotic (clindamycin phosphate) and/or keratolytic (miscrosponged benzoyl peroxide). |
WO2008093346A2 (en) * | 2007-02-01 | 2008-08-07 | Sol-Gel Technologies Ltd. | Compositions for topical application comprising a peroxide and retinoid |
FR2921257B1 (en) * | 2007-09-21 | 2009-11-06 | Exsymol Sa | TOPICAL USE OF THIAZOLIDINE DERIVATIVES FROM THE CONSEQUENCES OF OXIDATIVE SKIN STRESS |
US8632816B2 (en) | 2007-12-17 | 2014-01-21 | Elc Management, Llc | Compositions comprising solid particles entrapped in collapsed polymeric microspheres, and methods of making the same |
US20090155371A1 (en) * | 2007-12-17 | 2009-06-18 | Sojka Milan F | Compositions Comprising Solid Particles Entrapped In Collapsed Polymeric Microspheres, And Methods Of Making The Same |
JP2011510999A (en) * | 2008-02-01 | 2011-04-07 | アンコル インターナショナル コーポレイション | Improved skin whitening composition |
US20100040696A1 (en) * | 2008-08-12 | 2010-02-18 | Ilse Sente | Composite Particles Having An Antioxidant-Based Protective System, And Topical Compositions Comprising The Same |
WO2010030636A1 (en) * | 2008-09-12 | 2010-03-18 | Amcol International Corporation | Low ph retinoid topical compositions |
EP2391332A4 (en) * | 2009-01-29 | 2015-06-17 | Amcol International Corp | Matte skin finish compositions |
KR101080186B1 (en) * | 2010-06-21 | 2011-11-07 | 주식회사 필라이트솔루션 | Improved led lamp |
JP5950428B2 (en) | 2010-08-05 | 2016-07-13 | 日東電工株式会社 | Composition for regenerating normal tissue from fibrotic tissue |
WO2013091684A1 (en) | 2011-12-20 | 2013-06-27 | Oriflame Research And Development Ltd. | Compounds with anti-aging activities |
WO2013124820A1 (en) | 2012-02-21 | 2013-08-29 | Ranbaxy Laboratories Limited | Composition comprising a retinoid and benzoyl peroxide |
FR2991177B1 (en) | 2012-06-01 | 2014-12-19 | Galderma Res & Dev | TOPICAL COMPOSITIONS, CONTAINING RETINOID, EMULSION TYPE EMULSION IN WATER WITHOUT EMULSIFIER |
FR2991180B1 (en) | 2012-06-01 | 2014-06-13 | Galderma Res & Dev | EMULSION - FREE EMULSION - TYPE TOPICAL COMPOSITIONS BASED ON STABILIZING PARTICLES. |
FR2991176B1 (en) | 2012-06-01 | 2014-12-19 | Galderma Res & Dev | TOPICAL COMPOSITIONS CONTAINING SOLUBILIZED RETINOID OF HYDROGLYCOLIC GEL TYPE |
US9084778B2 (en) | 2012-06-01 | 2015-07-21 | Galderma Research & Development | Topical compositions containing a retinoid of the oil-in-water emulsion type |
US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
JP6340162B2 (en) | 2012-12-20 | 2018-06-06 | 日東電工株式会社 | Apoptosis inducer |
MY183106A (en) * | 2013-03-15 | 2021-02-15 | Laboratory Skin Care Inc | Fine dry particulate retinoid active agent compostions and topical formulations including the same |
US9976142B2 (en) | 2014-04-02 | 2018-05-22 | Nitto Denko Corporation | Targeting molecule and a use thereof |
CA2943733C (en) | 2014-04-07 | 2022-03-01 | Nitto Denko Corporation | Polymer-based hydrotropes for hydrophobic drug delivery |
KR101950693B1 (en) * | 2014-07-24 | 2019-02-21 | 주식회사 엘지생활건강 | Microneedle comprising retinol or retinol derivative |
CN106146734B (en) * | 2015-03-31 | 2018-07-20 | 中国石油化工股份有限公司 | A kind of coupling agent and its application and atactic butadiene styrene copolymer and preparation method thereof |
CA2996022C (en) | 2015-08-20 | 2021-01-05 | Sol-Gel Technologies Ltd. | Compositions for topical application comprising benzoyl peroxide and adapalene |
WO2017180440A1 (en) | 2016-04-11 | 2017-10-19 | Amcol International Corporation | Delivery system based on a natural microparticle for use in personal care and other topical applications |
WO2017184868A1 (en) | 2016-04-20 | 2017-10-26 | Duke University | Compositions, systems and methods for encapsulation and delivery of a substance |
WO2019068288A1 (en) | 2017-10-04 | 2019-04-11 | Berlimed International Research Gmbh | Product containing active substance and active substance matrix for transdermal active substance delivery and production and use thereof and active substance matrix and production and use thereof |
CN113164368B (en) * | 2018-12-04 | 2023-06-13 | 株式会社Lg生活健康 | High-content and sustained-release retinoid capsule and wrinkle-improving composition containing same |
US20220287946A1 (en) * | 2021-03-11 | 2022-09-15 | Peace Out Inc. | Anhydrous skin care composition comprising retinol and/or bakuchiol |
CN117202889A (en) * | 2021-04-16 | 2023-12-08 | 帝斯曼知识产权资产管理有限公司 | Retinol preparation (II) |
WO2022219016A1 (en) * | 2021-04-16 | 2022-10-20 | Dsm Ip Assets B.V. | Retinol formulation (i) |
Family Cites Families (17)
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US3906108A (en) * | 1973-10-12 | 1975-09-16 | Johnson & Johnson | Stabilized tretinoin cream emulsion |
US4247547A (en) * | 1979-03-19 | 1981-01-27 | Johnson & Johnson | Tretinoin in a gel vehicle for acne treatment |
US4603146A (en) * | 1984-05-16 | 1986-07-29 | Kligman Albert M | Methods for retarding the effects of aging of the skin |
US4877805A (en) * | 1985-07-26 | 1989-10-31 | Kligman Albert M | Methods for treatment of sundamaged human skin with retinoids |
US4826828A (en) * | 1985-04-22 | 1989-05-02 | Avon Products, Inc. | Composition and method for reducing wrinkles |
US5145675A (en) * | 1986-03-31 | 1992-09-08 | Advanced Polymer Systems, Inc. | Two step method for preparation of controlled release formulations |
US5089269A (en) * | 1987-11-07 | 1992-02-18 | Shiseido Company Ltd. | Cosmetic containing fine soft microcapsules |
ZA892859B (en) * | 1988-04-22 | 1989-12-27 | Advanced Polymer Systems Inc | Porous particles in preparations involving immiscible phases |
DE68917429T2 (en) * | 1988-11-16 | 1995-02-23 | Advanced Polymer Systems Inc | Cationic preparations for topical use. |
US5156843A (en) * | 1989-03-20 | 1992-10-20 | Advanced Polymer Systems, Inc. | Fabric impregnated with functional substances for controlled release |
US5073365A (en) * | 1989-06-01 | 1991-12-17 | Advanced Polymer Systems | Clinical and personal care articles enhanced by lubricants and adjuvants |
JP2980978B2 (en) * | 1989-10-03 | 1999-11-22 | アドバンスド ポリマー システムズ,インコーポレイティド | Erodible macroporous hydrogel particles and their preparation |
JP3014780B2 (en) * | 1990-01-29 | 2000-02-28 | ジヨンソン・アンド・ジヨンソン・コンシユーマー・プロダクツ・インコーポレーテツド | Skin care composition |
FR2666015B1 (en) * | 1990-08-23 | 1994-11-10 | Oreal | COSMETIC AND / OR DERMOPHARMACEUTICAL COMPOSITION CONTAINING RETINOUIC ACID OR DERIVATIVES THEREOF FOR TREATING HAIR OR SCALP. |
JP3435510B2 (en) * | 1991-06-27 | 2003-08-11 | ジヨンソン・アンド・ジヨンソン・コンシユーマー・プロダクツ・インコーポレーテツド | Skin care composition |
KR100295030B1 (en) * | 1992-07-13 | 2001-09-17 | 겜마 아키라 | Skin external composition |
GR1002207B (en) * | 1992-08-06 | 1996-03-27 | Johnson & Johnson Consumer | Skin care compositions containing imidazoles. |
-
1995
- 1995-12-29 US US08/581,126 patent/US5851538A/en not_active Expired - Lifetime
-
1996
- 1996-07-03 AU AU58310/96A patent/AU697584B2/en not_active Ceased
- 1996-07-16 DE DE69617181T patent/DE69617181T2/en not_active Expired - Lifetime
- 1996-07-16 ES ES96111446T patent/ES2168414T3/en not_active Expired - Lifetime
- 1996-07-16 AT AT96111446T patent/ATE209032T1/en active
- 1996-07-16 PT PT96111446T patent/PT781551E/en unknown
- 1996-07-16 EP EP96111446A patent/EP0781551B1/en not_active Expired - Lifetime
- 1996-07-16 DK DK96111446T patent/DK0781551T3/en active
- 1996-08-29 CA CA002184433A patent/CA2184433C/en not_active Expired - Lifetime
- 1996-12-11 JP JP8331305A patent/JP2960022B2/en not_active Expired - Fee Related
- 1996-12-27 KR KR1019960073537A patent/KR100262117B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE69617181D1 (en) | 2002-01-03 |
KR970032851A (en) | 1997-07-22 |
EP0781551B1 (en) | 2001-11-21 |
KR100262117B1 (en) | 2000-07-15 |
EP0781551A1 (en) | 1997-07-02 |
JP2960022B2 (en) | 1999-10-06 |
US5851538A (en) | 1998-12-22 |
CA2184433C (en) | 2000-01-18 |
ES2168414T3 (en) | 2002-06-16 |
DK0781551T3 (en) | 2002-05-21 |
AU5831096A (en) | 1997-07-03 |
PT781551E (en) | 2002-04-29 |
ATE209032T1 (en) | 2001-12-15 |
JPH09183722A (en) | 1997-07-15 |
DE69617181T2 (en) | 2002-06-06 |
AU697584B2 (en) | 1998-10-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20160829 |